The more decisions we’re asked to make, the less cognitive capacity we have available to assess the alternatives and make good, nuanced choices. ~Caroline Webb

We’re now knee-deep into the holiday season. But like a portion of the population, I’m still focused on the illusive time of year known as “open enrollment.” I’m part of the population who does not benefit from a group health insurance plan. I’m also at a point that I knew I would face sooner rather than later. I have a grandfathered health insurance plan, which means I have had most of the benefits similar to a group plan. However, the premiums have increased dramatically, to say the least.

I have felt as if I’ve been riding a freight train headed for the edge of a cliff and I’m trying to calculate the very last moment that I can jump off the train before it catapults off the edge of a mountain. The signal, at least for me, is that in the coming year I would be paying more for my health insurance than my housing expenses, if I choose to keep my current plan and hang on to that freight train for one more year. Or, do I make the decision to jump off, and what are my options?

I’m turning to the wisdom of Caroline Webb to help me make that decision. What she suggests in her book How to Have a Good Day is practical advice that leaders could use to make a multitude of decisions. Here are three points that I think are especially helpful.

• Notice when your automatic system is talking. If you’re saying to yourself something like, “It’s obviously…” “Everyone agrees.” “There’s only one real option.” then your automatic system may be making the decision as opposed to thoughtful consideration.
• Adopt a cross-check routine. Any one of these questions could become your cross-check. “What would be another way of seeing this?” “If you had to raise a concern, what would you say?” “What would be another option, and what do its advantages tell me?” “If this goes horribly wrong, what will have caused that?”
• Resolve dilemmas with great ease. Ask “What could I do?” rather than “What should I do?”

Putting into practice the tools of strategic planning – post-it notes – I’ll answer these questions with as many options that come to mind and post them up on the wall. Then I’ll cluster common themes, step back, and see what feels like the best option.

Then I’ll heed Webb’s fourth suggestion.

• Watch out for system fatigue. If you feel impatient, distracted, or clumsy, take a mindful pause.

After sleeping on it, talking with a number of friends who are in a similar situation, and revisiting the options with a clear head, then I’ll make a decision.

Health insurance is my current dilemma, as a leader, you may have your own dilemma or list of decisions as you close out 2017 and look to 2018. Maybe Webb’s insights can help you, as well, make some wise decisions that are good, nuanced choices.